110704-45-5

Basic information

• Product Name: 5-(ChloroMethyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole
• Synonyms: 5-(ChloroMethyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole
• CAS NO: 110704-45-5
• Molecular Formula: C₉H₆ClFN₂O
• Molecular Weight: 212.6081432
• Mol File: 110704-45-5.mol

Chemical Properties

• Boiling Point: 319.0±52.0 °C(Predicted)
• Appearance: /
• Density: 1.364±0.06 g/cm3(Predicted)
• PKA: -3.23±0.44(Predicted)
• CAS DataBase Reference: 5-(ChloroMethyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(ChloroMethyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole(110704-45-5)
• EPA Substance Registry System: 5-(ChloroMethyl)-3-(2-fluorophenyl)-1,2,4-oxadiazole(110704-45-5)

Safety Data

• Hazardous Substances Data: 110704-45-5(Hazardous Substances Data)

Upstream product

• 75907-83-4 (Z)-2-fluoro-N'-hydroxybenzimidamide 
• 79-04-9 chloroacetyl chloride 
• 844498-75-5 C₉H₈ClFN₂O₂ 

Downstream Products

• 110703-57-6 {3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-4-oxo-3,4-dihydro-phthalazin-1-yl}-acetic acid 

Relevant articles and documents

New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity

A series of 3- and 5-aryl-1,2,4-oxadiazole derivatives were prepared and tested for anticonvulsant activity in a variety of models. These 1,2,4-oxadiazoles exhibit considerable activity in both pentylenetetrazole (PTZ) and maximal electroshock seizure (MES) models. Compound 10 was protective in the PTZ model in rats with an oral ED50 of 25.5 mg/kg and in the MES model in rats with an oral ED50 of 14.6 mg/kg. Neurotoxicity (rotarod) was observed with an ED50 of 335 mg/kg. We found several oxadiazoles that acted as selective GABA potentiating compounds with no interaction to the benzodiazepine binding site.

The discovery of a selective, high affinity A2B adenosine receptor antagonist for the potential treatment of asthma

Adenosine has been suggested to play a role in asthma, possibly via activation of A2B adenosine receptors on mast cells and other pulmonary cells. We describe our initial efforts to discover a xanthine based selective A2B AdoR antagonist that resulted in the discovery of CVT-5440, a high affinity A2B AdoR antagonist with good selectivity (A2B AdoR Ki = 50 nM, selectivity A1 > 200: A2A > 200: A3 > 167).

Potent, orally active aldose reductase inhibitors related to zopolrestat: Surrogates for benzothiazole side chain

A broad structure-activity program was undertaken in search of effective surrogates for the key benzothiazole side chain of the potent aldose reductase inhibitor, zopolrestat (1). A structure-driven approach was pursued, which spanned exploration of three areas: (1) 5/6 fused heterocycles such as benzoxazole, benzothiophene, benzofuran, and imidazopyridine; (2) 5- membered heterocycles, including oxadiazole, oxazole, thiazole, and thiadiazole, with pendant aryl groups, and (3) thioanilide as a formal equivalent of benzothiazole. Several benzoxazole- and 1,2,4-oxadiazole- derived analogues were found to be potent inhibitors of aldose reductase from human placenta and were orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications. 3,4-Dihydro-4- oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1-phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10-9 M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg. Compound 139, 3,4-dihydro-4-oxo-3-[[(2-fluorophenyl)-1,2,4- oxadiazol-5-yl]methyl]-1-phthalazineacetic acid, with IC50 -8 M, caused a 69% reduction in sorbitol accumulation in rat sciatic nerve at an oral dose of 25 mg/kg. The thioanilide side chain featured in 3-[2-[[3- (trifluoromethyl)phenyl]amino]-2-thioxoethyl]-3,4-dihydro-4-oxo-1- phthalazineacetic acid (195) proved to be an effective surrogate for benzothiazole. Compound 195 was highly potent in vitro (IC50 = 5.2 x 10-8 M) but did not show oral activity when tested at 100 mg/kg. Additional structure-activity relationships encompassing a variety of heterocyclic side chains are discussed.